diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index b6bb7c866..3ae094dcd 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -80,7 +80,7 @@ jobs:
       env:
         CIBW_ARCHS_MACOS: x86_64 universal2 arm64
         CIBW_BUILD_FRONTEND: 'build[uv]'
-        CIBW_ENABLE: "cpython-prerelease cpython-freethreading pypy"
+        CIBW_ENABLE: "cpython-prerelease cpython-freethreading pypy graalpy"
 
     - name: Run a sample build (GitHub Action, only)
       uses: ./
diff --git a/README.md b/README.md
index 12b328001..2d9af6b11 100644
--- a/README.md
+++ b/README.md
@@ -36,14 +36,15 @@ While cibuildwheel itself requires a recent Python version to run (we support th
 | PyPy 3.9 v7.3  | ✅ | ✅  | ✅  | N/A | N/A | ✅¹ | ✅¹  | ✅¹ | N/A | N/A | N/A | N/A | N/A |
 | PyPy 3.10 v7.3 | ✅ | ✅  | ✅  | N/A | N/A | ✅¹ | ✅¹  | ✅¹ | N/A | N/A | N/A | N/A | N/A |
 | PyPy 3.11 v7.3 | ✅ | ✅  | ✅  | N/A | N/A | ✅¹ | ✅¹  | ✅¹ | N/A | N/A | N/A | N/A | N/A |
+| GraalPy 24.2   | ✅ | ✅  | ✅  | N/A | N/A | ✅¹ | N/A  | ✅¹ | N/A | N/A | N/A | N/A | N/A |
 
-<sup>¹ PyPy is only supported for manylinux wheels.</sup><br>
+<sup>¹ PyPy & GraalPy are only supported for manylinux wheels.</sup><br>
 <sup>² Windows arm64 support is experimental.</sup><br>
 <sup>³ Free-threaded mode requires opt-in using [`CIBW_ENABLE`](https://cibuildwheel.pypa.io/en/stable/options/#enable).</sup><br>
 <sup>⁴ Experimental, not yet supported on PyPI, but can be used directly in web deployment. Use `--platform pyodide` to build.</sup><br>
 <sup>⁵ manylinux armv7l support is experimental. As there are no RHEL based image for this architecture, it's using an Ubuntu based image instead.</sup><br>
 
-- Builds manylinux, musllinux, macOS 10.9+ (10.13+ for Python 3.12+), and Windows wheels for CPython and PyPy
+- Builds manylinux, musllinux, macOS 10.9+ (10.13+ for Python 3.12+), and Windows wheels for CPython, PyPy, and GraalPy
 - Works on GitHub Actions, Azure Pipelines, Travis CI, AppVeyor, CircleCI, GitLab CI, and Cirrus CI
 - Bundles shared library dependencies on Linux and macOS through [auditwheel](https://github.com/pypa/auditwheel) and [delocate](https://github.com/matthew-brett/delocate)
 - Runs your library's tests against the wheel-installed version of your library
diff --git a/azure-pipelines.yml b/azure-pipelines.yml
index eaf93958e..1cc707fd9 100644
--- a/azure-pipelines.yml
+++ b/azure-pipelines.yml
@@ -6,7 +6,7 @@ pr:
 
 jobs:
 - job: linux_311
-  timeoutInMinutes: 120
+  timeoutInMinutes: 180
   pool: {vmImage: 'Ubuntu-22.04'}
   steps:
     - task: UsePythonVersion@0
@@ -20,6 +20,7 @@ jobs:
 
 - job: macos_311
   pool: {vmImage: 'macOS-13'}
+  timeoutInMinutes: 120
   steps:
     - task: UsePythonVersion@0
       inputs:
diff --git a/bin/update_pythons.py b/bin/update_pythons.py
index 7b8ea1474..75de60a64 100755
--- a/bin/update_pythons.py
+++ b/bin/update_pythons.py
@@ -5,6 +5,7 @@
 import difflib
 import logging
 import operator
+import re
 import tomllib
 from collections.abc import Mapping, MutableMapping
 from pathlib import Path
@@ -44,13 +45,19 @@ class ConfigWinPP(TypedDict):
     url: str
 
 
+class ConfigWinGP(TypedDict):
+    identifier: str
+    version: str
+    url: str
+
+
 class ConfigApple(TypedDict):
     identifier: str
     version: str
     url: str
 
 
-AnyConfig = ConfigWinCP | ConfigWinPP | ConfigApple
+AnyConfig = ConfigWinCP | ConfigWinPP | ConfigWinGP | ConfigApple
 
 
 # The following set of "Versions" classes allow the initial call to the APIs to
@@ -106,6 +113,72 @@ def update_version_windows(self, spec: Specifier) -> ConfigWinCP | None:
         )
 
 
+class GraalPyVersions:
+    def __init__(self) -> None:
+        response = requests.get("https://api.github.com/repos/oracle/graalpython/releases")
+        response.raise_for_status()
+
+        releases = response.json()
+        gp_version_re = re.compile(r"-(\d+\.\d+\.\d+)$")
+        cp_version_re = re.compile(r"Python (\d+\.\d+(?:\.\d+)?)")
+        for release in releases:
+            m = gp_version_re.search(release["tag_name"])
+            if m:
+                release["graalpy_version"] = Version(m.group(1))
+            m = cp_version_re.search(release["body"])
+            if m:
+                release["python_version"] = Version(m.group(1))
+
+        self.releases = [r for r in releases if "graalpy_version" in r and "python_version" in r]
+
+    def update_version(self, identifier: str, spec: Specifier) -> AnyConfig:
+        if "x86_64" in identifier or "amd64" in identifier:
+            arch = "x86_64"
+        elif "arm64" in identifier or "aarch64" in identifier:
+            arch = "aarch64"
+        else:
+            msg = f"{identifier} not supported yet on GraalPy"
+            raise RuntimeError(msg)
+
+        releases = [r for r in self.releases if spec.contains(r["python_version"])]
+        releases = sorted(releases, key=lambda r: r["graalpy_version"])
+
+        if not releases:
+            msg = f"GraalPy {arch} not found for {spec}!"
+            raise RuntimeError(msg)
+
+        release = releases[-1]
+        version = release["python_version"]
+        gpversion = release["graalpy_version"]
+
+        if "macosx" in identifier:
+            arch = "x86_64" if "x86_64" in identifier else "arm64"
+            config = ConfigApple
+            platform = "macos"
+        elif "win" in identifier:
+            arch = "aarch64" if "arm64" in identifier else "x86_64"
+            config = ConfigWinGP
+            platform = "windows"
+        else:
+            msg = "GraalPy provides downloads for macOS and Windows and is included for manylinux"
+            raise RuntimeError(msg)
+
+        arch = "amd64" if arch == "x86_64" else "aarch64"
+        ext = "zip" if "win" in identifier else "tar.gz"
+        (url,) = (
+            rf["browser_download_url"]
+            for rf in release["assets"]
+            if rf["name"].endswith(f"{platform}-{arch}.{ext}")
+            and rf["name"].startswith(f"graalpy-{gpversion.major}")
+        )
+
+        return config(
+            identifier=identifier,
+            version=f"{version.major}.{version.minor}",
+            url=url,
+        )
+
+
 class PyPyVersions:
     def __init__(self, arch_str: ArchStr):
         response = requests.get("https://downloads.python.org/pypy/versions.json")
@@ -294,6 +367,8 @@ def __init__(self) -> None:
 
         self.ios_cpython = CPythonIOSVersions()
 
+        self.graalpy = GraalPyVersions()
+
     def update_config(self, config: MutableMapping[str, str]) -> None:
         identifier = config["identifier"]
         version = Version(config["version"])
@@ -311,6 +386,8 @@ def update_config(self, config: MutableMapping[str, str]) -> None:
                     config_update = self.macos_pypy.update_version_macos(spec)
                 elif "macosx_arm64" in identifier:
                     config_update = self.macos_pypy_arm64.update_version_macos(spec)
+            elif identifier.startswith("gp"):
+                config_update = self.graalpy.update_version(identifier, spec)
         elif "t-win32" in identifier and identifier.startswith("cp"):
             config_update = self.windows_t_32.update_version_windows(spec)
         elif "win32" in identifier and identifier.startswith("cp"):
@@ -322,6 +399,8 @@ def update_config(self, config: MutableMapping[str, str]) -> None:
                 config_update = self.windows_64.update_version_windows(spec)
             elif identifier.startswith("pp"):
                 config_update = self.windows_pypy_64.update_version_windows(spec)
+            elif identifier.startswith("gp"):
+                config_update = self.graalpy.update_version(identifier, spec)
         elif "t-win_arm64" in identifier and identifier.startswith("cp"):
             config_update = self.windows_t_arm64.update_version_windows(spec)
         elif "win_arm64" in identifier and identifier.startswith("cp"):
diff --git a/cibuildwheel/logger.py b/cibuildwheel/logger.py
index 321352e8c..80c2fb02e 100644
--- a/cibuildwheel/logger.py
+++ b/cibuildwheel/logger.py
@@ -243,6 +243,8 @@ def build_description_from_identifier(identifier: str) -> str:
         build_description += "CPython"
     elif python_interpreter == "pp":
         build_description += "PyPy"
+    elif python_interpreter == "gp":
+        build_description += "GraalPy"
     else:
         msg = f"unknown python {python_interpreter!r}"
         raise Exception(msg)
diff --git a/cibuildwheel/platforms/macos.py b/cibuildwheel/platforms/macos.py
index 4b4a064d8..420e16139 100644
--- a/cibuildwheel/platforms/macos.py
+++ b/cibuildwheel/platforms/macos.py
@@ -103,7 +103,7 @@ def get_python_configurations(
     # skip builds as required by BUILD/SKIP
     python_configurations = [c for c in python_configurations if build_selector(c.identifier)]
 
-    # filter-out some cross-compilation configs with PyPy:
+    # filter-out some cross-compilation configs with PyPy and GraalPy:
     # can't build arm64 on x86_64
     # rosetta allows to build x86_64 on arm64
     if platform.machine() == "x86_64":
@@ -111,7 +111,7 @@ def get_python_configurations(
         python_configurations = [
             c
             for c in python_configurations
-            if not (c.identifier.startswith("pp") and c.identifier.endswith("arm64"))
+            if not (c.identifier.startswith(("pp", "gp")) and c.identifier.endswith("arm64"))
         ]
         removed_elements = python_configurations_before - set(python_configurations)
         if removed_elements:
@@ -191,6 +191,22 @@ def install_pypy(tmp: Path, url: str) -> Path:
     return installation_path / "bin" / "pypy3"
 
 
+def install_graalpy(tmp: Path, url: str) -> Path:
+    graalpy_archive = url.rsplit("/", 1)[-1]
+    extension = ".tar.gz"
+    assert graalpy_archive.endswith(extension)
+    installation_path = CIBW_CACHE_PATH / graalpy_archive[: -len(extension)]
+    with FileLock(str(installation_path) + ".lock"):
+        if not installation_path.exists():
+            downloaded_archive = tmp / graalpy_archive
+            download(url, downloaded_archive)
+            installation_path.mkdir(parents=True)
+            # GraalPy top-folder name is inconsistent with archive name
+            call("tar", "-C", installation_path, "--strip-components=1", "-xzf", downloaded_archive)
+            downloaded_archive.unlink()
+    return installation_path / "bin" / "graalpy"
+
+
 def setup_python(
     tmp: Path,
     python_configuration: PythonConfiguration,
@@ -212,6 +228,8 @@ def setup_python(
 
     elif implementation_id.startswith("pp"):
         base_python = install_pypy(tmp, python_configuration.url)
+    elif implementation_id.startswith("gp"):
+        base_python = install_graalpy(tmp, python_configuration.url)
     else:
         msg = "Unknown Python implementation"
         raise ValueError(msg)
diff --git a/cibuildwheel/platforms/windows.py b/cibuildwheel/platforms/windows.py
index a63890644..91e72404b 100644
--- a/cibuildwheel/platforms/windows.py
+++ b/cibuildwheel/platforms/windows.py
@@ -123,6 +123,20 @@ def install_pypy(tmp: Path, arch: str, url: str) -> Path:
     return installation_path / "python.exe"
 
 
+def install_graalpy(tmp: Path, url: str) -> Path:
+    zip_filename = url.rsplit("/", 1)[-1]
+    extension = ".zip"
+    assert zip_filename.endswith(extension)
+    installation_path = CIBW_CACHE_PATH / zip_filename[: -len(extension)]
+    with FileLock(str(installation_path) + ".lock"):
+        if not installation_path.exists():
+            graalpy_zip = tmp / zip_filename
+            download(url, graalpy_zip)
+            # Extract to the parent directory because the zip file still contains a directory
+            extract_zip(graalpy_zip, installation_path.parent)
+    return installation_path / "bin" / "graalpy.exe"
+
+
 def setup_setuptools_cross_compile(
     tmp: Path,
     python_configuration: PythonConfiguration,
@@ -239,6 +253,8 @@ def setup_python(
     elif implementation_id.startswith("pp"):
         assert python_configuration.url is not None
         base_python = install_pypy(tmp, python_configuration.arch, python_configuration.url)
+    elif implementation_id.startswith("gp"):
+        base_python = install_graalpy(tmp, python_configuration.url or "")
     else:
         msg = "Unknown Python implementation"
         raise ValueError(msg)
@@ -314,6 +330,49 @@ def setup_python(
         setup_setuptools_cross_compile(tmp, python_configuration, python_libs_base, env)
         setup_rust_cross_compile(tmp, python_configuration, python_libs_base, env)
 
+    if implementation_id.startswith("gp"):
+        # GraalPy fails to discover compilers, setup the relevant environment
+        # variables. Adapted from
+        # https://github.com/microsoft/vswhere/wiki/Start-Developer-Command-Prompt
+        # Remove when https://github.com/oracle/graalpython/issues/492 is fixed.
+        vcpath = subprocess.check_output(
+            [
+                Path(os.environ["PROGRAMFILES(X86)"])
+                / "Microsoft Visual Studio"
+                / "Installer"
+                / "vswhere.exe",
+                "-products",
+                "*",
+                "-latest",
+                "-property",
+                "installationPath",
+            ],
+            text=True,
+        ).strip()
+        log.notice(f"Discovering Visual Studio for GraalPy at {vcpath}")
+        env.update(
+            dict(
+                [
+                    envvar.strip().split("=", 1)
+                    for envvar in subprocess.check_output(
+                        [
+                            f"{vcpath}\\Common7\\Tools\\vsdevcmd.bat",
+                            "-no_logo",
+                            "-arch=amd64",
+                            "-host_arch=amd64",
+                            "&&",
+                            "set",
+                        ],
+                        shell=True,
+                        text=True,
+                        env=env,
+                    )
+                    .strip()
+                    .split("\n")
+                ]
+            )
+        )
+
     return base_python, env
 
 
@@ -342,6 +401,7 @@ def build(options: Options, tmp_path: Path) -> None:
         for config in python_configurations:
             build_options = options.build_options(config.identifier)
             build_frontend = build_options.build_frontend or BuildFrontendConfig("build")
+
             use_uv = build_frontend.name == "build[uv]" and can_use_uv(config)
             log.build_start(config.identifier)
 
@@ -390,6 +450,22 @@ def build(options: Options, tmp_path: Path) -> None:
                     build_frontend, build_options.build_verbosity, build_options.config_settings
                 )
 
+                if (
+                    config.identifier.startswith("gp")
+                    and build_frontend.name == "build"
+                    and "--no-isolation" not in extra_flags
+                    and "-n" not in extra_flags
+                ):
+                    # GraalPy fails to discover its standard library when a venv is created
+                    # from a virtualenv seeded executable. See
+                    # https://github.com/oracle/graalpython/issues/491 and remove this once
+                    # fixed upstream.
+                    log.notice(
+                        "Disabling build isolation to workaround GraalPy bug. If the build fails, consider using pip or build[uv] as build frontend."
+                    )
+                    shell("graalpy -m pip install setuptools wheel", env=env)
+                    extra_flags = [*extra_flags, "-n"]
+
                 build_env = env.copy()
                 if pip_version is not None:
                     build_env["VIRTUALENV_PIP"] = pip_version
@@ -414,6 +490,7 @@ def build(options: Options, tmp_path: Path) -> None:
                 elif build_frontend.name == "build" or build_frontend.name == "build[uv]":
                     if use_uv and "--no-isolation" not in extra_flags and "-n" not in extra_flags:
                         extra_flags.append("--installer=uv")
+
                     call(
                         "python",
                         "-m",
diff --git a/cibuildwheel/resources/build-platforms.toml b/cibuildwheel/resources/build-platforms.toml
index d2ad15e09..d77ac1e2d 100644
--- a/cibuildwheel/resources/build-platforms.toml
+++ b/cibuildwheel/resources/build-platforms.toml
@@ -18,6 +18,7 @@ python_configurations = [
   { identifier = "pp39-manylinux_x86_64", version = "3.9", path_str = "/opt/python/pp39-pypy39_pp73" },
   { identifier = "pp310-manylinux_x86_64", version = "3.10", path_str = "/opt/python/pp310-pypy310_pp73" },
   { identifier = "pp311-manylinux_x86_64", version = "3.11", path_str = "/opt/python/pp311-pypy311_pp73" },
+  { identifier = "gp242-manylinux_x86_64", version = "3.11", path_str = "/opt/python/graalpy311-graalpy242_311_native" },
   { identifier = "cp38-manylinux_aarch64", version = "3.8", path_str = "/opt/python/cp38-cp38" },
   { identifier = "cp39-manylinux_aarch64", version = "3.9", path_str = "/opt/python/cp39-cp39" },
   { identifier = "cp310-manylinux_aarch64", version = "3.10", path_str = "/opt/python/cp310-cp310" },
@@ -57,6 +58,7 @@ python_configurations = [
   { identifier = "pp39-manylinux_aarch64", version = "3.9", path_str = "/opt/python/pp39-pypy39_pp73" },
   { identifier = "pp310-manylinux_aarch64", version = "3.10", path_str = "/opt/python/pp310-pypy310_pp73" },
   { identifier = "pp311-manylinux_aarch64", version = "3.11", path_str = "/opt/python/pp311-pypy311_pp73" },
+  { identifier = "gp242-manylinux_aarch64", version = "3.11", path_str = "/opt/python/graalpy311-graalpy242_311_native" },
   { identifier = "pp38-manylinux_i686", version = "3.8", path_str = "/opt/python/pp38-pypy38_pp73" },
   { identifier = "pp39-manylinux_i686", version = "3.9", path_str = "/opt/python/pp39-pypy39_pp73" },
   { identifier = "pp310-manylinux_i686", version = "3.10", path_str = "/opt/python/pp310-pypy310_pp73" },
@@ -143,6 +145,8 @@ python_configurations = [
   { identifier = "pp310-macosx_arm64", version = "3.10", url = "https://downloads.python.org/pypy/pypy3.10-v7.3.19-macos_arm64.tar.bz2" },
   { identifier = "pp311-macosx_x86_64", version = "3.11", url = "https://downloads.python.org/pypy/pypy3.11-v7.3.19-macos_x86_64.tar.bz2" },
   { identifier = "pp311-macosx_arm64", version = "3.11", url = "https://downloads.python.org/pypy/pypy3.11-v7.3.19-macos_arm64.tar.bz2" },
+  { identifier = "gp242-macosx_x86_64", version = "3.11", url = "https://github.com/oracle/graalpython/releases/download/graal-24.2.0/graalpy-24.2.0-macos-amd64.tar.gz" },
+  { identifier = "gp242-macosx_arm64", version = "3.11", url = "https://github.com/oracle/graalpython/releases/download/graal-24.2.0/graalpy-24.2.0-macos-aarch64.tar.gz" },
 ]
 
 [windows]
@@ -171,6 +175,7 @@ python_configurations = [
   { identifier = "pp39-win_amd64", version = "3.9", arch = "64", url = "https://downloads.python.org/pypy/pypy3.9-v7.3.16-win64.zip" },
   { identifier = "pp310-win_amd64", version = "3.10", arch = "64", url = "https://downloads.python.org/pypy/pypy3.10-v7.3.19-win64.zip" },
   { identifier = "pp311-win_amd64", version = "3.11", arch = "64", url = "https://downloads.python.org/pypy/pypy3.11-v7.3.19-win64.zip" },
+  { identifier = "gp242-win_amd64", version = "3.11", arch = "64", url = "https://github.com/oracle/graalpython/releases/download/graal-24.2.0/graalpy-24.2.0-windows-amd64.zip" },
 ]
 
 [pyodide]
diff --git a/cibuildwheel/selector.py b/cibuildwheel/selector.py
index 98c7a6601..48578712d 100644
--- a/cibuildwheel/selector.py
+++ b/cibuildwheel/selector.py
@@ -33,6 +33,7 @@ class EnableGroup(StrEnum):
     CPythonPrerelease = "cpython-prerelease"
     PyPy = "pypy"
     CPythonExperimentalRiscV64 = "cpython-experimental-riscv64"
+    GraalPy = "graalpy"
 
     @classmethod
     def all_groups(cls) -> frozenset["EnableGroup"]:
@@ -75,6 +76,8 @@ def __call__(self, build_id: str) -> bool:
             build_id, "*_riscv64"
         ):
             return False
+        if EnableGroup.GraalPy not in self.enable and fnmatch(build_id, "gp*"):
+            return False
 
         should_build = selector_matches(self.build_config, build_id)
         should_skip = selector_matches(self.skip_config, build_id)
diff --git a/docs/options.md b/docs/options.md
index 9d906b0c9..5006d8e28 100644
--- a/docs/options.md
+++ b/docs/options.md
@@ -323,6 +323,7 @@ values are:
 - `cpython-experimental-riscv64`: Enable experimental riscv64 builds. Those builds
   are disabled by default as they can't be uploaded to PyPI and a PEP will most likely
   be required before this can happen.
+- `graalpy`: Enable GraalPy.
 
 
 !!! caution
diff --git a/test/conftest.py b/test/conftest.py
index 8c0c9504c..f2b575df0 100644
--- a/test/conftest.py
+++ b/test/conftest.py
@@ -56,9 +56,8 @@ def docker_warmup(request: pytest.FixtureRequest) -> None:
     images = [build_options.manylinux_images[arch] for arch in archs] + [
         build_options.musllinux_images[arch] for arch in archs
     ]
-    # exclude GraalPy as it's not a target for cibuildwheel
     command = (
-        "manylinux-interpreters ensure $(manylinux-interpreters list 2>/dev/null | grep -v graalpy) &&"
+        "manylinux-interpreters ensure-all &&"
         "cpython3.13 -m pip download -d /tmp setuptools wheel pytest"
     )
     for image in images:
diff --git a/test/test_abi_variants.py b/test/test_abi_variants.py
index ec529849d..5c7c27f54 100644
--- a/test/test_abi_variants.py
+++ b/test/test_abi_variants.py
@@ -41,9 +41,9 @@ def test_abi3(tmp_path):
     actual_wheels = utils.cibuildwheel_run(
         project_dir,
         add_env={
-            # free_threaded and PyPy do not have a Py_LIMITED_API equivalent, just build one of those
+            # free_threaded, GraalPy, and PyPy do not have a Py_LIMITED_API equivalent, just build one of those
             # also limit the number of builds for test performance reasons
-            "CIBW_BUILD": f"cp39-* cp310-* pp310-* {single_python_tag}-* cp313t-*"
+            "CIBW_BUILD": f"cp39-* cp310-* pp310-* gp242-* {single_python_tag}-* cp313t-*"
         },
     )
 
@@ -59,7 +59,11 @@ def test_abi3(tmp_path):
         expected_wheels = [
             w.replace("cp310-cp310", "cp310-abi3")
             for w in expected_wheels
-            if "-cp39" in w or "-cp310" in w or "-pp310" in w or "-cp313t" in w
+            if "-cp39" in w
+            or "-cp310" in w
+            or "-pp310" in w
+            or "-graalpy242" in w
+            or "-cp313t" in w
         ]
     assert set(actual_wheels) == set(expected_wheels)
 
diff --git a/test/test_before_all.py b/test/test_before_all.py
index a46031ee7..c7ec86240 100644
--- a/test/test_before_all.py
+++ b/test/test_before_all.py
@@ -38,8 +38,8 @@ def test(tmp_path):
 
     # build the wheels
     before_all_command = (
-        """python -c "import os, sys;open('{project}/text_info.txt', 'w').write('sample text '+os.environ.get('TEST_VAL', ''))" && """
-        '''python -c "import sys; open('{project}/python_prefix.txt', 'w').write(sys.prefix)"'''
+        """python -c "import os, pathlib, sys; pathlib.Path('{project}/text_info.txt').write_text('sample text '+os.environ.get('TEST_VAL', ''))" && """
+        '''python -c "import pathlib, sys; pathlib.Path('{project}/python_prefix.txt').write_text(sys.prefix)"'''
     )
     actual_wheels = utils.cibuildwheel_run(
         project_dir,
diff --git a/test/test_before_build.py b/test/test_before_build.py
index 19a770133..9494de7bd 100644
--- a/test/test_before_build.py
+++ b/test/test_before_build.py
@@ -41,8 +41,8 @@ def test(tmp_path):
     project_with_before_build_asserts.generate(project_dir)
 
     before_build = (
-        """python -c "import sys; open('{project}/pythonversion_bb.txt', 'w').write(sys.version)" && """
-        f'''python -c "import sys; open('{{project}}/pythonprefix_bb.txt', 'w').write({SYS_PREFIX})"'''
+        """python -c "import pathlib, sys; pathlib.Path('{project}/pythonversion_bb.txt').write_text(sys.version)" && """
+        f'''python -c "import pathlib, sys; pathlib.Path('{{project}}/pythonprefix_bb.txt').write_text({SYS_PREFIX})"'''
     )
     frontend = "build"
     if utils.platform != "pyodide":
diff --git a/test/test_before_test.py b/test/test_before_test.py
index 7e766abaa..a3700f843 100644
--- a/test/test_before_test.py
+++ b/test/test_before_test.py
@@ -7,7 +7,7 @@
 from pathlib import Path
 from unittest import TestCase
 
-PROJECT_DIR = Path(__file__).joinpath("..", "..").resolve()
+PROJECT_DIR = Path(__file__).parent.parent.resolve()
 
 
 class TestBeforeTest(TestCase):
@@ -39,8 +39,8 @@ def test(tmp_path, build_frontend_env):
     test_projects.new_c_project().generate(test_project_dir)
 
     before_test_steps = [
-        '''python -c "import os, sys; open('{project}/pythonversion_bt.txt', 'w').write(sys.version)"''',
-        '''python -c "import os, sys; open('{project}/pythonprefix_bt.txt', 'w').write(sys.prefix)"''',
+        '''python -c "import pathlib, sys; pathlib.Path('{project}/pythonversion_bt.txt').write_text(sys.version)"''',
+        '''python -c "import pathlib, sys; pathlib.Path('{project}/pythonprefix_bt.txt').write_text(sys.prefix)"''',
     ]
 
     if utils.platform == "pyodide":
@@ -63,7 +63,9 @@ def test(tmp_path, build_frontend_env):
             # the 'false ||' bit is to ensure this command runs in a shell on
             # mac/linux.
             "CIBW_TEST_COMMAND": f"false || {utils.invoke_pytest()} ./test",
-            "CIBW_TEST_COMMAND_WINDOWS": "pytest ./test",
+            # pytest fails on GraalPy 24.2.0 on Windows so we skip it there
+            # until https://github.com/oracle/graalpython/issues/490 is fixed
+            "CIBW_TEST_COMMAND_WINDOWS": "where graalpy || pytest ./test",
             **build_frontend_env,
         },
     )
diff --git a/test/test_dependency_versions.py b/test/test_dependency_versions.py
index b8d80f3bc..d4b9416f3 100644
--- a/test/test_dependency_versions.py
+++ b/test/test_dependency_versions.py
@@ -128,6 +128,17 @@ def test_dependency_constraints(method, tmp_path, build_frontend_env_nouv):
 
     build_environment = {}
 
+    if (
+        utils.platform == "windows"
+        and method == "file"
+        and build_frontend_env_nouv["CIBW_BUILD_FRONTEND"] == "build"
+    ):
+        # GraalPy fails to discover its standard library when a venv is created
+        # from a virtualenv seeded executable. See
+        # https://github.com/oracle/graalpython/issues/491 and remove this once
+        # fixed upstream.
+        build_frontend_env_nouv["CIBW_SKIP"] = "gp*"
+
     for package_name, version in tool_versions.items():
         env_name = f"EXPECTED_{package_name.upper()}_VERSION"
         build_environment[env_name] = version
@@ -147,4 +158,13 @@ def test_dependency_constraints(method, tmp_path, build_frontend_env_nouv):
     # also check that we got the right wheels
     expected_wheels = utils.expected_wheels("spam", "0.1.0")
 
+    if (
+        utils.platform == "windows"
+        and method == "file"
+        and build_frontend_env_nouv["CIBW_BUILD_FRONTEND"] == "build"
+    ):
+        # See reference to https://github.com/oracle/graalpython/issues/491
+        # above
+        expected_wheels = [w for w in expected_wheels if "graalpy" not in w]
+
     assert set(actual_wheels) == set(expected_wheels)
diff --git a/test/test_pep518.py b/test/test_pep518.py
index 2147520f9..c861f0da3 100644
--- a/test/test_pep518.py
+++ b/test/test_pep518.py
@@ -33,11 +33,26 @@ def test_pep518(tmp_path, build_frontend_env):
     project_dir = tmp_path / "project"
     basic_project.generate(project_dir)
 
+    # GraalPy fails to discover its standard library when a venv is created
+    # from a virtualenv seeded executable. See
+    # https://github.com/oracle/graalpython/issues/491 and remove this once
+    # fixed upstream.
+    if build_frontend_env["CIBW_BUILD_FRONTEND"] == "build" and utils.platform == "windows":
+        build_frontend_env["CIBW_SKIP"] = "gp*"
+
     # build the wheels
     actual_wheels = utils.cibuildwheel_run(project_dir, add_env=build_frontend_env)
 
     # check that the expected wheels are produced
     expected_wheels = utils.expected_wheels("spam", "0.1.0")
+
+    # GraalPy fails to discover its standard library when a venv is created
+    # from a virtualenv seeded executable. See
+    # https://github.com/oracle/graalpython/issues/491 and remove this once
+    # fixed upstream.
+    if build_frontend_env["CIBW_BUILD_FRONTEND"] == "build" and utils.platform == "windows":
+        expected_wheels = [w for w in expected_wheels if "graalpy" not in w]
+
     assert set(actual_wheels) == set(expected_wheels)
 
     # These checks ensure an extra file is not created when using custom
diff --git a/test/test_testing.py b/test/test_testing.py
index 16f00aa60..9b7364f99 100644
--- a/test/test_testing.py
+++ b/test/test_testing.py
@@ -81,7 +81,9 @@ def test(tmp_path):
             # the 'false ||' bit is to ensure this command runs in a shell on
             # mac/linux.
             "CIBW_TEST_COMMAND": f"false || {utils.invoke_pytest()} ./test",
-            "CIBW_TEST_COMMAND_WINDOWS": "COLOR 00 || pytest ./test",
+            # pytest fails on GraalPy 24.2.0 on Windows so we skip it there
+            # until https://github.com/oracle/graalpython/issues/490 is fixed
+            "CIBW_TEST_COMMAND_WINDOWS": "COLOR 00 || where graalpy || pytest ./test",
         },
     )
 
@@ -102,7 +104,9 @@ def test_extras_require(tmp_path):
             # the 'false ||' bit is to ensure this command runs in a shell on
             # mac/linux.
             "CIBW_TEST_COMMAND": f"false || {utils.invoke_pytest()} ./test",
-            "CIBW_TEST_COMMAND_WINDOWS": "COLOR 00 || pytest ./test",
+            # pytest fails on GraalPy 24.2.0 on Windows so we skip it there
+            # until https://github.com/oracle/graalpython/issues/490 is fixed
+            "CIBW_TEST_COMMAND_WINDOWS": "COLOR 00 || where graalpy || pytest ./test",
         },
         single_python=True,
     )
@@ -134,7 +138,9 @@ def test_dependency_groups(tmp_path):
             # the 'false ||' bit is to ensure this command runs in a shell on
             # mac/linux.
             "CIBW_TEST_COMMAND": f"false || {utils.invoke_pytest()} ./test",
-            "CIBW_TEST_COMMAND_WINDOWS": "COLOR 00 || pytest ./test",
+            # pytest fails on GraalPy 24.2.0 on Windows so we skip it there
+            # until https://github.com/oracle/graalpython/issues/490 is fixed
+            "CIBW_TEST_COMMAND_WINDOWS": "COLOR 00 || where graalpy || pytest ./test",
         },
         single_python=True,
     )
@@ -189,7 +195,9 @@ def test_bare_pytest_invocation(tmp_path: Path, test_runner: str) -> None:
         add_env={
             "CIBW_TEST_REQUIRES": "pytest" if test_runner == "pytest" else "",
             "CIBW_TEST_COMMAND": (
-                "python -m pytest"
+                # pytest fails on GraalPy 24.2.0 on Windows so we skip it there
+                # until https://github.com/oracle/graalpython/issues/490 fixed
+                "graalpy.exe -c 1 || python -m pytest"
                 if test_runner == "pytest"
                 else "python -m unittest discover test spam_test.py"
             ),
@@ -211,7 +219,9 @@ def test_test_sources(tmp_path):
         add_env={
             "CIBW_TEST_REQUIRES": "pytest",
             "CIBW_TEST_COMMAND": "pytest",
-            "CIBW_TEST_COMMAND_WINDOWS": "pytest",
+            # pytest fails on GraalPy 24.2.0 on Windows so we skip it there
+            # until https://github.com/oracle/graalpython/issues/490 is fixed
+            "CIBW_TEST_COMMAND_WINDOWS": "where graalpy || pytest",
             "CIBW_TEST_SOURCES": "test",
         },
     )
diff --git a/test/utils.py b/test/utils.py
index e05d3a2dd..957ee7295 100644
--- a/test/utils.py
+++ b/test/utils.py
@@ -55,7 +55,7 @@ def cibuildwheel_get_build_identifiers(
     cmd = [sys.executable, "-m", "cibuildwheel", "--print-build-identifiers", str(project_path)]
     if env is None:
         env = os.environ.copy()
-    env["CIBW_ENABLE"] = "cpython-freethreading pypy"
+    env["CIBW_ENABLE"] = "cpython-freethreading pypy graalpy"
     if prerelease_pythons:
         env["CIBW_ENABLE"] += " cpython-prerelease"
 
@@ -257,6 +257,10 @@ def _expected_wheels(
                 "pp310-pypy310_pp73",
                 "pp311-pypy311_pp73",
             ]
+        if machine_arch in ["x86_64", "AMD64", "aarch64", "arm64"]:
+            python_abi_tags += [
+                "graalpy311-graalpy242_311_native",
+            ]
 
     if single_python:
         python_tag = "cp{}{}-".format(*SINGLE_PYTHON_VERSION)
@@ -286,7 +290,7 @@ def _expected_wheels(
                         for manylinux_version in manylinux_versions
                     )
                 ]
-            if len(musllinux_versions) > 0 and not python_abi_tag.startswith("pp"):
+            if len(musllinux_versions) > 0 and not python_abi_tag.startswith(("pp", "graalpy")):
                 platform_tags.append(
                     ".".join(
                         f"{musllinux_version}_{machine_arch}"
diff --git a/unit_test/linux_build_steps_test.py b/unit_test/linux_build_steps_test.py
index cd295a5e9..aa4363c13 100644
--- a/unit_test/linux_build_steps_test.py
+++ b/unit_test/linux_build_steps_test.py
@@ -24,7 +24,7 @@ def test_linux_container_split(tmp_path: Path, monkeypatch: pytest.MonkeyPatch)
                 manylinux-x86_64-image = "normal_container_image"
                 manylinux-i686-image = "normal_container_image"
                 build = "*-manylinux_x86_64"
-                skip = "pp*"
+                skip = "[gp]p*"
                 archs = "x86_64 i686"
 
                 [[tool.cibuildwheel.overrides]]
diff --git a/unit_test/main_tests/main_options_test.py b/unit_test/main_tests/main_options_test.py
index 48723213b..66ee4c952 100644
--- a/unit_test/main_tests/main_options_test.py
+++ b/unit_test/main_tests/main_options_test.py
@@ -423,9 +423,9 @@ def test_debug_traceback(monkeypatch, method, capfd):
 @pytest.mark.parametrize("method", ["unset", "command_line", "env_var"])
 def test_enable(method, intercepted_build_args, monkeypatch):
     if method == "command_line":
-        monkeypatch.setattr(sys, "argv", [*sys.argv, "--enable", "pypy"])
+        monkeypatch.setattr(sys, "argv", [*sys.argv, "--enable", "pypy", "--enable", "graalpy"])
     elif method == "env_var":
-        monkeypatch.setenv("CIBW_ENABLE", "pypy")
+        monkeypatch.setenv("CIBW_ENABLE", "pypy graalpy")
 
     main()
 
@@ -434,18 +434,20 @@ def test_enable(method, intercepted_build_args, monkeypatch):
     if method == "unset":
         assert enable_groups == frozenset()
     else:
-        assert enable_groups == frozenset([EnableGroup.PyPy])
+        assert enable_groups == frozenset([EnableGroup.PyPy, EnableGroup.GraalPy])
 
 
 def test_enable_arg_inherits(intercepted_build_args, monkeypatch):
-    monkeypatch.setenv("CIBW_ENABLE", "pypy")
+    monkeypatch.setenv("CIBW_ENABLE", "pypy graalpy")
     monkeypatch.setattr(sys, "argv", [*sys.argv, "--enable", "cpython-prerelease"])
 
     main()
 
     enable_groups = intercepted_build_args.args[0].globals.build_selector.enable
 
-    assert enable_groups == frozenset((EnableGroup.PyPy, EnableGroup.CPythonPrerelease))
+    assert enable_groups == frozenset(
+        (EnableGroup.PyPy, EnableGroup.GraalPy, EnableGroup.CPythonPrerelease)
+    )
 
 
 def test_enable_arg_error_message(monkeypatch, capsys):
diff --git a/unit_test/option_prepare_test.py b/unit_test/option_prepare_test.py
index 4a24190c1..d5dc7d191 100644
--- a/unit_test/option_prepare_test.py
+++ b/unit_test/option_prepare_test.py
@@ -14,7 +14,7 @@
 from cibuildwheel.util import file
 
 DEFAULT_IDS = {"cp38", "cp39", "cp310", "cp311", "cp312", "cp313"}
-ALL_IDS = DEFAULT_IDS | {"cp313t", "pp38", "pp39", "pp310", "pp311"}
+ALL_IDS = DEFAULT_IDS | {"cp313t", "pp38", "pp39", "pp310", "pp311", "gp242"}
 
 
 @pytest.fixture
@@ -103,7 +103,7 @@ def test_build_with_override_launches(monkeypatch, tmp_path):
 [tool.cibuildwheel]
 manylinux-x86_64-image = "manylinux_2_28"
 musllinux-x86_64-image = "musllinux_1_2"
-enable = ["pypy", "cpython-freethreading"]
+enable = ["pypy", "graalpy", "cpython-freethreading"]
 
 # Before Python 3.10, use manylinux2014
 [[tool.cibuildwheel.overrides]]
@@ -155,6 +155,7 @@ def test_build_with_override_launches(monkeypatch, tmp_path):
             "pp39",
             "pp310",
             "pp311",
+            "gp242",
         }
     }
     assert kwargs["options"].build_options("cp39-manylinux_x86_64").before_all == ""
@@ -176,6 +177,7 @@ def test_build_with_override_launches(monkeypatch, tmp_path):
             "pp39",
             "pp310",
             "pp311",
+            "gp242",
         ]
     }
 
@@ -185,14 +187,16 @@ def test_build_with_override_launches(monkeypatch, tmp_path):
     assert kwargs["container"]["oci_platform"] == OCIPlatform.i386
 
     identifiers = {x.identifier for x in kwargs["platform_configs"]}
-    assert identifiers == {f"{x}-manylinux_i686" for x in ALL_IDS}
+    assert identifiers == {f"{x}-manylinux_i686" for x in ALL_IDS if "gp" not in x}
 
     kwargs = build_in_container.call_args_list[4][1]
     assert "quay.io/pypa/musllinux_1_2_x86_64" in kwargs["container"]["image"]
     assert kwargs["container"]["cwd"] == PurePosixPath("/project")
     assert kwargs["container"]["oci_platform"] == OCIPlatform.AMD64
     identifiers = {x.identifier for x in kwargs["platform_configs"]}
-    assert identifiers == {f"{x}-musllinux_x86_64" for x in ALL_IDS if "pp" not in x}
+    assert identifiers == {
+        f"{x}-musllinux_x86_64" for x in ALL_IDS if "pp" not in x and "gp" not in x
+    }
 
     kwargs = build_in_container.call_args_list[5][1]
     assert "quay.io/pypa/musllinux_1_2_i686" in kwargs["container"]["image"]
@@ -200,4 +204,6 @@ def test_build_with_override_launches(monkeypatch, tmp_path):
     assert kwargs["container"]["oci_platform"] == OCIPlatform.i386
 
     identifiers = {x.identifier for x in kwargs["platform_configs"]}
-    assert identifiers == {f"{x}-musllinux_i686" for x in ALL_IDS if "pp" not in x}
+    assert identifiers == {
+        f"{x}-musllinux_i686" for x in ALL_IDS if "pp" not in x and "gp" not in x
+    }